- "Why am I not surprised? Wherever Darhk is, you're not too far away."
- —Sara to Merlyn
|When a new Time Aberration is discovered by the Legends, they find themselves headed to 1927 Chicago. The Legends quickly realize that they have been set up by Eobard Thawne, Damien Darhk and the newest member of the Legion of Doom, Malcolm Merlyn. While everyone is trying to help fix what they think is the mission, Jax encourages a reluctant Stein to share his secret with the other Legends. Stein is taken captive and Sara must make the tough choice of either stopping the Legion of Doom or saving Stein. Meanwhile, Rory gets an unexpected visitor and is not sure how to handle it.|
Thawne, Darhk and Malcolm arrive in Chicago, 1927, and ally with Al Capone.
The team get alerted by the aberration and arrive, managing to save Eliot Ness from getting killed by Capone. They put Ness in the care of Gideon and decide to complete his mission to secure history.
They infiltrate a club owned by Capone. Sara and Martin are abducted. He tells her about Lily. The team rescues the duo and brings them to the Waverider, where it is revealed that Thawne has imposed himself as Martin.
Thawne opens the door for Malcolm and Capone's operatives. Sara yields the amulet in exchange for Martin's location.
The latter is saved from Capone. Sara agrees not to erase Lily from the timeline. With the completed amulet, Thawne shows Darhk and Malcolm a hologram that is compass meant to help find the Spear of Destiny, which the former believes can be used to "rewrite reality itself".
He also states that they need to find Rip. The final scene shows that Rip is working as a movie director in Los Angeles, directing an actor who looks very much like Ray Palmer. in 1967.
Meanwhile, Mick starts having hallucinations of Leonard, who blames him for helping the team. Mick also starts becoming more intimate with Amaya.
Preparation ran from October 3 until October 12, 2016, with a break for Canadian Thanksgiving on October 10. Shooting ran from October 13 until October 24, 2016.
- The title of the episode is a reference to a quote from the 1987 gangster film The Untouchables, in which Jimmy Malone describes to Eliot Ness how to get Al Capone, describing it as "the Chicago way". Also the character of Ness says his famous true line "Never stop fighting until the fight is done!"
- While posing as an F.B.I. agent, Ray uses the alias "Bob De Niro". This is a reference to actor Robert De Niro, who played Al Capone in The Untouchables.
- Ray does an impression Jimmy Malone (played by Sean Connery) with his line "Isn't that just like a thug. Brings a tommy gun to an ion blaster fight."
- It wasn't revealed which year Malcolm Merlyn is from in this episode. However, he was seen with his cybernetic hand, which means that this is a version of Malcolm Merlyn from some time after "".
- The device Eobard Thawne used to take the appearance of Martin Stein is the same device he used to take the appearance of Harrison Wells. This is the first appearance of the device since episode, "".
- Jax tells Ray and Nate that "Stein's about to kill Sara in the library" (when Thawne had already disguised himself as Stein using the aforementioned device). Ray's answer to this is "with the rope or the candlestick?" which is a reference to the game, Clue (known outside North America as "Cluedo") where players have to solve a murder, deducing which suspect is the killer, which room the murder happened in, and which of several potential weapons was used. (This also implies that the board game might actually be on the ship.)
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